Pyridine → HCID 22905634, 화합물

HRID 1488458노트

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HRID 1488458 반응식
[OH:1][C:2]1[C:3]([CH3:13])=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[NH:7][CH2:6][CH:5]2[CH3:12].N1C=CC=CC=1.[C:20](Cl)(=[O:24])[CH:21]([CH3:23])[CH3:22]>C(Cl)Cl>[C:20]([N:7]1[C:8]2[C:4](=[C:3]([CH3:13])[C:2]([OH:1])=[C:10]([CH3:11])[CH:9]=2)[CH:5]([CH3:12])[CH2:6]1)(=[O:24])[CH:21]([CH3:23])[CH3:22]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 62325Isobutyryl chlorideHCID 22905653HCID 22905653, 화합물

생성물 1

HCID 22905634HCID 22905634, 화합물수율 73.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To an ice-cold solution of indoline 10 (160 mg, 0.9 mmol) dissolved in methylene chloride (4 mL) and kept under an argon atmosphere were added sequentially pyridine (1 mL) and isobutyryl chloride (0.I mL, 9 mmol); the mixture was stirred over the range of 0° C. to room temperature for some 17 h. The mixture was diluted with methylene chloride, washed with brine and dried (MgSO4). Removal of solvents followed by purification of the residue using 1:9 ethyl acetate:hexanes as eluent afforded the desired N-isobutyryl-5-hydroxy-3,4,6-trimethylindoline (11b, 163 mg, 73% yield) as a colorless solid, mp 123°-125° C. Spectral data: 1H NMR: δ1.1-1.25 (m, 9H), 2.17 (s, 3H), 2.20 (s, 3H), 2.72 (quintet, 1H, J=6.5 Hz), 3.35 (t, 1H, J=6.5 Hz), 3.78 (dd, 1H, J=10.1, 1.0 Hz), 4.13 (t, 1H, J=9.1 Hz), 7.95 (s, 1H); 13C NMR: δ 11.9, 16.5, 18.8, 19.3, 20.7, 33.1, 34.0, 56.3, 116.8, 119.5, 122.1, 134.1, 135.0, 148.8, 175.0; HRMS: calcd. for C15H21NO2 247.1523, fnd. 247.1573. Anal: calcd. for C15H21NO2C, 72.85, H, 8.55, N, 5.66, fnd. C, 72.63, H, 8.59, N, 5.60.

후처리

  1. washwashed with brine
  2. dry with materialdried (MgSO4)
  3. customRemoval of solvents
  4. customfollowed by purification of the residue

출처 및 근거

ORD 기록
ord-fc3887e276024ae9bd645069b917c0d0
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05674876

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